But seriously, it is a lot harder to get stuff off your shoes than your feet. And usually you watch where you go anyway. Also I kinda enjoy being able to just walk through puddles and being completely dry again after about five steps.

As for broken glass, you'd be surprised how fast you get calluses that glass will hardly ever pierce when walking over it. In the first month or so it might happen, but after a while you don't even feel them anymore. The hot asphalt in the summer is way worse. But as long as you keep walking neither that nor snow and ice really are a problem.